# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ic21528
_database_code_depnum_ccdc_archive 'CCDC 2190441'
loop_
_audit_author_name
_audit_author_address
'Ping-Jyun Sung'
;National Museum of Marine Biology and Aquarium
Taiwan
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        napalilactone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H21 Cl O3'
_chemical_formula_weight         272.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2367(2)
_cell_length_b                   9.9002(3)
_cell_length_c                   17.2237(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1404.51(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    19846
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.47

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.599
_exptl_crystal_size_mid          0.512
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39483
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.365
_diffrn_reflns_theta_max         29.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4100
_reflns_number_gt                3494
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.6043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4100
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38179(10) 0.33622(9) 0.89907(5) 0.0494(2) Uani 1 1 d . . . . .
O1 O 0.6770(2) 0.43119(18) 0.80724(11) 0.0339(4) Uani 1 1 d . . . . .
O2 O 0.6649(3) 0.6458(2) 0.84524(16) 0.0522(6) Uani 1 1 d . . . . .
O3 O 0.9380(3) 0.0891(3) 0.63888(15) 0.0569(6) Uani 1 1 d . . . . .
C1 C 0.5186(4) 0.2349(3) 0.84004(17) 0.0359(6) Uani 1 1 d . . . . .
H1 H 0.468307 0.245186 0.788558 0.043 Uiso 1 1 d R U . . .
C2 C 0.5167(4) 0.0896(3) 0.8671(2) 0.0462(7) Uani 1 1 d . . . . .
H2A H 0.404292 0.054255 0.865681 0.055 Uiso 1 1 calc R U . . .
H2B H 0.556549 0.084139 0.921188 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6252(5) 0.0052(3) 0.8140(2) 0.0466(7) Uani 1 1 d . . . . .
H3A H 0.577029 0.003107 0.761357 0.056 Uiso 1 1 calc R U . . .
H3B H 0.628325 -0.088757 0.833692 0.056 Uiso 1 1 calc R U . . .
C4 C 0.7994(4) 0.0592(3) 0.80843(17) 0.0388(6) Uani 1 1 d . . . . .
H4 H 0.845390 0.011878 0.763335 0.047 Uiso 1 1 d R U . . .
C5 C 0.8022(3) 0.2119(3) 0.78502(15) 0.0310(5) Uani 1 1 d . . . . .
C6 C 0.6896(3) 0.2959(2) 0.84037(15) 0.0308(5) Uani 1 1 d . . . . .
C7 C 0.6902(4) 0.5293(3) 0.86135(19) 0.0380(6) Uani 1 1 d . . . . .
C8 C 0.7389(4) 0.4704(3) 0.93801(18) 0.0415(6) Uani 1 1 d . . . . .
H8A H 0.655259 0.488812 0.977895 0.050 Uiso 1 1 calc R U . . .
H8B H 0.843544 0.508891 0.955633 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7549(4) 0.3191(3) 0.92374(17) 0.0401(6) Uani 1 1 d . . . . .
H9A H 0.689981 0.267550 0.961995 0.048 Uiso 1 1 calc R U . . .
H9B H 0.869702 0.290436 0.927718 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7348(4) 0.2283(3) 0.70151(16) 0.0367(6) Uani 1 1 d . . . . .
H10A H 0.618(5) 0.189(4) 0.697(2) 0.044 Uiso 1 1 d . U . . .
H10B H 0.722(4) 0.326(4) 0.690(2) 0.044 Uiso 1 1 d . U . . .
C11 C 0.8219(4) 0.1640(3) 0.63388(17) 0.0400(6) Uani 1 1 d . . . . .
C12 C 0.7503(6) 0.1982(4) 0.5560(2) 0.0622(10) Uani 1 1 d . . . . .
H12A H 0.807836 0.148074 0.515385 0.093 Uiso 1 1 calc R U . . .
H12B H 0.761426 0.295401 0.546516 0.093 Uiso 1 1 calc R U . . .
H12C H 0.635140 0.173526 0.555366 0.093 Uiso 1 1 calc R U . . .
C13 C 0.8973(5) 0.0216(4) 0.8807(2) 0.0542(9) Uani 1 1 d . . . . .
H13A H 0.844101 0.058696 0.926864 0.081 Uiso 1 1 calc R U . . .
H13B H 1.007163 0.058941 0.876343 0.081 Uiso 1 1 calc R U . . .
H13C H 0.903562 -0.076958 0.885095 0.081 Uiso 1 1 calc R U . . .
C14 C 0.9742(4) 0.2701(3) 0.7853(2) 0.0456(7) Uani 1 1 d . . . . .
H14A H 1.042501 0.218494 0.749419 0.068 Uiso 1 1 calc R U . . .
H14B H 1.019404 0.264339 0.837831 0.068 Uiso 1 1 calc R U . . .
H14C H 0.970744 0.364846 0.768881 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.819(3) . ?
O1 C7 1.351(3) . ?
O1 C6 1.460(3) . ?
O2 C7 1.205(4) . ?
O3 C11 1.213(4) . ?
C1 C2 1.511(4) . ?
C1 C6 1.533(4) . ?
C2 C3 1.528(5) . ?
C3 C4 1.534(5) . ?
C4 C13 1.529(4) . ?
C4 C5 1.565(4) . ?
C5 C14 1.529(4) . ?
C5 C10 1.550(4) . ?
C5 C6 1.568(4) . ?
C6 C9 1.550(4) . ?
C7 C8 1.498(5) . ?
C8 C9 1.523(4) . ?
C10 C11 1.509(4) . ?
C11 C12 1.504(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C6 112.6(2) . . ?
C2 C1 C6 112.5(3) . . ?
C2 C1 Cl1 110.3(2) . . ?
C6 C1 Cl1 110.48(18) . . ?
C1 C2 C3 109.3(2) . . ?
C2 C3 C4 113.2(3) . . ?
C13 C4 C3 111.0(3) . . ?
C13 C4 C5 115.9(3) . . ?
C3 C4 C5 111.5(2) . . ?
C14 C5 C10 107.2(2) . . ?
C14 C5 C4 112.1(2) . . ?
C10 C5 C4 109.6(2) . . ?
C14 C5 C6 110.2(2) . . ?
C10 C5 C6 107.3(2) . . ?
C4 C5 C6 110.3(2) . . ?
O1 C6 C1 107.1(2) . . ?
O1 C6 C9 104.5(2) . . ?
C1 C6 C9 112.4(2) . . ?
O1 C6 C5 106.9(2) . . ?
C1 C6 C5 109.4(2) . . ?
C9 C6 C5 115.9(2) . . ?
O2 C7 O1 121.1(3) . . ?
O2 C7 C8 128.5(3) . . ?
O1 C7 C8 110.5(2) . . ?
C7 C8 C9 105.3(2) . . ?
C8 C9 C6 105.4(2) . . ?
C11 C10 C5 120.1(2) . . ?
O3 C11 C12 120.7(3) . . ?
O3 C11 C10 125.3(3) . . ?
C12 C11 C10 114.0(3) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.052

